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July 24, 2025
David Norelid, Technical Alignment Manager
If you're still holding off on moving your organization to Windows 11, you're not alone. Between hardware compatibility requirements, software dependencies, and the classic "if it ain't broke, don't fixit" mindset, plenty of teams have delayed the upgrade.
But with time running out and Windows 10 end-of-life looming in October 2025, staying put is no longer a viable option.
Here’s what to consider before diving in:
Windows 11 brought significant changes to Microsoft’s minimum hardware requirements specifically with mandates for TPM 2.0 and newer-generation CPUs. Machines that might feel perfectly fine today may not even qualify for the upgrade.
We recommend:
1. Using Microsoft’s PC Health Check or scripting a scan across your device fleet. Your management tools should be able to produce a hardware report for you that target CPU model (8th Gen and newer) and TPM version (2.0 and up).
2. Flagging any systems that aren’t eligible, and planning replacements now—not when you're under deadline.
3. Audit legacy software because older apps or plugins can cause stability or compatibility issues under Windows 11.
Windows 11 doesn’t support 32-bit systems or 16-bit applications. If you’re still using either, you won’t be able to upgrade directly—and may need new hardware or a virtualization setup instead.
Don’t assume everything will “just work.” Many organizations rely on a mix of modern and legacy tools that can behave differently under Windows 11.
For engineering teams, this is especially true. We’ve helped firms test:
• OpenRoads Designer and MicroStation for snapping, referencing, and plug-in behavior
• Driver and firmware updates – older hardware may break or lag without updated drivers under Windows 11
• Custom apps and file-sharing platforms used in project delivery
Build a test group with real users from multiple departments especially those that rely on GPU-intensive design workflows. It’s not just about checking if the software opens, it’s about whether it performs and integrates the way your team needs.
Once testing is complete, don’t rush the deployment. A staged, well-communicated rollout helps reduce disruption and gives you room to catch and fix issues before they become widespread and your end-users panic.
Here’s what we typically recommend:
1. Roll out in waves – Begin with your internal IT team, then move to general users, and finally your most critical departments.
2. Train your team – Windows 11 might look familiar, but we’ve found that taskbar changes and settings menu adjustments are the #1 source of user complaints. Providing short training videos or quick reference guides can dramatically cut down on help desk tickets.
3. Have a fallback plan – Even with the best prep, things happen. Having a rollback option ensures you’re not stuck if something breaks during rollout
With a new OS comes new security features and policy controls. Before you roll out Windows 11 organization-wide, it’s a good idea to:
1. Review and update your Group Policy Objects (GPOs) for compatibility with Windows 11
2. Audit any device compliance baselines you're enforcing through Intune or other MDM tools
3. Take advantage of new security features like Windows Hello, Credential Guard, and Application Control
That’s because… you do.
Windows 10 reaches end-of-life in October 2025, which means no more security updates, bug fixes, or Microsoft support. If you're in a regulated environment or tied to public sector contracts like TxDOT, this isn’t optional—it’s mission-critical.
And if you plan to stay on Windows 10 past that date? Be prepared to pay for extended support and we don’t mean a small bump. Microsoft’s ESU (Extended Security Updates) program is notoriously expensive. You’ll be spending thousands just to stand still—and still won’t be fully compliant.
Once TxDOT budgets open back up in the coming months, it’ll be a firestorm. Everyone will be rushing to upgrade at once and that usually means hardware shortages, overloaded support teams, and rushed deployments, so DO NOT WAIT!
If you're an early Windows 11 adopter, you might still be running a version that’s already reached End of Life (EoL)—and you might not even realize it. Starting with Windows 10, Microsoft adopted a stepped upgrade model, releasing major versions in the second half of each year—hence the “H2” in names like 21H2, 22H2, and 23H2.
Many organizations have locked their deployments to specific versions for stability and compatibility reasons. But here’s the catch: support for Windows 11 21H2 ended back in October 2023 and both Windows11 22H2 and 23H2 (non-Enterprise editions) will reach EoL alongside Windows 10 in October 2025. Enterprise editions of 23H2 and newer will continue to receive support for at least another year.
Not sure which version you're on? Press Start, type "winver", and hit Enter. If you see 23H2, build 10.0.22631 or lower, it’s time to start planning your upgrade.
At 5 Factor, we help businesses migrate to the latest version of Windows 11 with zero disruption to your day-to-day operations. Don’t wait until the last minute—reach out now to start your upgrade the right way.
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